Methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(benzo-furazanyl)pyridine-3-carboxylate | 105567-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: Methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(benzo-furazanyl)pyridine-3-carboxylate
• 英文别名: methyl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-5-nitro-1,4-dihydropyridine-3-carboxylate
• CAS: 105567-84-8
• 化学式: C₁₅H₁₄N₄O₅
• 分子量: 330.3
• InChiKey: CWXJXZBBBDROHK-UHFFFAOYSA-N

物化性质

• 沸点：
  492.6±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  β-氨基巴豆酸甲酯 以 异丙醇 为溶剂， 反应 5.0h， 生成 Methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(benzo-furazanyl)pyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis and Voltage-Clamp Studies of Methyl 1,4-Dihydro-2,6-dimethyl-5-nitro-4-(benzofurazanyl)pyridine-3-carboxylate Racemates and Enantiomers and of Their Benzofuroxanyl Analogues

  摘要：

  Racemic methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(benzofurazanyl)pyridine-3-carboxylates(+/-)-10 and (+/-)-11 and their benzofuroxanyl analogues (+/-)-12 and (+/-)-13 were prepared using a modified Hantzsch reaction that involved the condensation of nitroacetone with methyl 3-aminocrotonate and the appropriate aldehydes. The racemic mixtures were resolved into the corresponding enantiomers. Whole-cell voltage-clamp studies on L-type Ca2+ channels expressed in a rat insulinoma cell line (RINm5F) showed that all the dextrorotatory antipodes were effective agonists of L-type Ca2+ currents, while the levorotatory ones were weak Ca2+ entry blockers. The (+)-enantiomer of benzofurazan-5'-yl derivative 11 demonstrated unusual activity in that, in addition to producing a potentiation of L-type currents, it interfered with the voltage-dependent gating of L-type channels by producing a net delay of their activation at low voltages. This compound represents an interesting tool to probe L-type Ca2+ channel structure and function.

  DOI：

  10.1021/jm980623b

文献信息

• Synthesis and Voltage-Clamp Studies of Methyl 1,4-Dihydro-2,6-dimethyl-5-nitro-4-(benzofurazanyl)pyridine-3-carboxylate Racemates and Enantiomers and of Their Benzofuroxanyl Analogues
  作者：Sonja Visentin、Pascale Amiel、Roberta Fruttero、Donatella Boschi、Christian Roussel、Laura Giusta、Emilio Carbone、Alberto Gasco

  DOI：10.1021/jm980623b

  日期：1999.4.22

  Racemic methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(benzofurazanyl)pyridine-3-carboxylates(+/-)-10 and (+/-)-11 and their benzofuroxanyl analogues (+/-)-12 and (+/-)-13 were prepared using a modified Hantzsch reaction that involved the condensation of nitroacetone with methyl 3-aminocrotonate and the appropriate aldehydes. The racemic mixtures were resolved into the corresponding enantiomers. Whole-cell voltage-clamp studies on L-type Ca2+ channels expressed in a rat insulinoma cell line (RINm5F) showed that all the dextrorotatory antipodes were effective agonists of L-type Ca2+ currents, while the levorotatory ones were weak Ca2+ entry blockers. The (+)-enantiomer of benzofurazan-5'-yl derivative 11 demonstrated unusual activity in that, in addition to producing a potentiation of L-type currents, it interfered with the voltage-dependent gating of L-type channels by producing a net delay of their activation at low voltages. This compound represents an interesting tool to probe L-type Ca2+ channel structure and function.